3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 68809475, compound

HRID 434303

Reaction equation

HRID 434303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[C@@H:27]([CH:28]=O)[CH2:26][O:25][C:24]1([CH3:31])[CH3:30])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.ClCCl>[C:16]([O:20][C:21]([N:23]1[C@@H:27]([CH2:28][N:13]2[CH2:14][CH2:15][CH:10]([C:8](=[O:9])[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:11][CH2:12]2)[CH2:26][O:25][C:24]1([CH3:30])[CH3:31])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68809475HCID 68809475, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-fluoro-phenyl)-piperidin-4-yl-methanone (3.5 g, 17 mmol) in dry tetrahydrofuran (50 ml) is added (R)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.9 g, 17 mmol) and sodium triacetoxyborohydride (5.4 g, 25 mmol), and the reaction mixture stirred for 18 hours at ambient temperature. The reaction mixture is filtered and the solvent evaporated to give a white solid. The solid is taken up in dichloromethane (50 ml) and washed with saturated sodium bicarbonate solution (50 ml), water (2×50 ml) and brine (50 ml). The organic phase is dried over magnesium sulphate and evaporated to afford the product, [MH]+420.9.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent evaporated
  3. customto give a white solid
  4. washwashed with saturated sodium bicarbonate solution (50 ml), water (2×50 ml) and brine (50 ml)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated
  7. customto afford the product, [MH]+420.9

Sources & evidence

ORD record
ord-bcb2009a4e644e87a58309e501982678
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Linked notes

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